Potassium Carbonate → 3-Ethynyl-5-nitropyridine

HRID 2271654Notes

Reaction equation

HRID 2271654 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:10]#[C:11][Si](C)(C)C)[CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+]>CO.C(OCC)(=O)C>[C:10]([C:8]1[CH:7]=[N:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1)#[CH:11]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 667157023-Nitro-5-((trimethylsilyl)ethynyl)pyridine

Product 1

HCID 747877233-Ethynyl-5-nitropyridineYield 74.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitro-5-((trimethylsilyl)ethynyl)pyridine (4.90 mmol) in MeOH (15 mL) was added K2CO3 (67 mg, 0.49 mmol). The mixture was stirred at rt for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and chromatographed (hexane/ethyl acetate) to afford the desired product (540 mg, 74% over two steps) as a light brown solid: 1H NMR (300 MHz, CDCl3) δ 9.39-9.38 (m, 1H), 8.99-8.98 (m, 1H), 8.56-8.54 (m, 1H), 3.40 (s, 1H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. customchromatographed (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-16c91cd5ad044b4f90dc44e268914df4
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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